KILL TONY Wiki

Sir Winston Pickles

🎤 6 appearances🏆 #84 most appearancesFirst: July 7, 2025Latest: May 18, 2026

Sir Winston Pickles has performed on Kill Tony 6 times. Every appearance below, with set summaries and timestamps.

Appearances

Kill Tony #770 Bucket Pull · May 18, 2026

Sir Winston delivers dark jokes about Boston Marathon bombing preparation, Nancy Grace's disappearance, and hitting a toddler with his shopping cart.

  • Takes longer than 7 days to prepare pressure cooker bomb
  • Nancy Grace disappeared from supermarkets
  • Deliberately hit toddler with shopping cart to teach lesson
Kill Tony #757 Bucket Pull · February 16, 2026

Evil clown character discusses sponsoring African child three years at 99 cents/week, credit card expired, child died, head sold to tourist, jokes about Olive Garden chef suicide in fryer.

  • Sponsored African child, credit expired, he died, head sold to tourist
  • Olive Garden worker starts as chef, ends as head chef (suicide)
Kill Tony #750 Bucket Pull · December 15, 2025

Sir Winston Pickles, a dark clown character, performs dark jokes about hitting an old lady, Christmas suicidality, drag racing in heels, and using Luminol spray instead of Christmas lights.

  • Hit a dear old lady instead of a deer
  • Only needs Luminol instead of Christmas lights due to murders
Kill Tony #741 Bucket Pull · October 13, 2025

Winston performs in whiteface makeup, opens with Ed Gein lampshade joke about wife/kids murders, neighbor chainsaw murder, school zone speeding joke, dyslexia joke blowback.

  • More fuckers on I35 than in Ed Gein's lampshade collection
  • Neighbor asked to borrow chainsaw day after murdering wife/kids with chainsaw; he lied about owning one
Kill Tony #732 Bucket Pull · August 4, 2025

Dark comedy about cell phones, marriages, and a wife who hanged herself while swinging. Dark clown persona delivering twisted observations with British accent.

  • Lost cell phone in Malaysian airplane mode.
  • Wife was a swinger, found her hanging herself.
  • Has mother's eyes in a mason jar.
Kill Tony #728 Bucket Pull · July 7, 2025

Sir Winston, a clown, discusses his age, staying in shape, a concerning interaction with a teenage jogger, and a Diana joke about the Mercedes-Benz.

  • His high school belt still fits around his neck at age 60.
  • Drives slowly behind teenage jogger with lights off to keep her safe.
  • Made Diana/Mercedes-Benz joke about the most beautiful Mercedes-Benz ever made.